Beilstein J. Org. Chem.2017,13, 1361–1367, doi:10.3762/bjoc.13.133
, Australia 10.3762/bjoc.13.133 Abstract Background: Crotonoil is the only commercial source of the diterpenoid phorbol (1a), the starting material for the semi-synthesis of various diesters extensively used in biomedical research to investigate cell function and to evaluate in vivo anti-inflammatory
activity. While efficient chemoselective esterification protocols have been developed for phorbol, its isolation from crotonoil is technically complicated, and involves extensive manipulation of very toxic materials like the oil or its native diterpenoid fraction.
Results: The preparation of a crude non
-irritant phorboid mixture from crotonoil was telescoped to only five operational steps, and phorbol could then be purified by gravity column chromatography and crystallization. Evidence is provided that two distinct phorboid chemotypes of crotonoil exist, differing in the relative proportion of type-A
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Graphical Abstract
Figure 1:
The major diterpene polyols from croton oil [phorbol (1a), 4α-phorbol (2), 4-deoxy-4α-phorbol (3a)]...